Boron trifluoride etherate → Cyclododecanecarboxaldehyde

HRID 37304

反応式

HRID 37304 の反応式
[O:1]1[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.CCOCC.CCCCCC.CCCCCC.C(OCC)(=O)C>CCOCC>[CH:3]1([CH:2]=[O:1])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 110198001-Oxaspiro[2.11]tetradecaneHCID 21226206Ethyl acetate hexane

生成物 1

HCID 78737Cyclododecanecarboxaldehyde収率 34%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To 5.0 g (25.5 mmol) of 1-oxaspiro[2.11]tetradecane in 50 ml of dry ether at 0° C. is slowly added 1.8 ml (2.1 g, 14.6 mmol) of boron trifluoride etherate. The ice bath is removed and after 15 minutes at room temperature the solution is partitioned between ether and saturated sodium bicarbonate. The organic phase is evaporated to give a clear oil. Flash chromatography over silica gel using a hexane to hexane:ethyl acetate (9:1) gradient give 1.6 g (34%) of a clear oil: NMR (CDCl3) δ 1.28-1.8 (m, 18H), 2.03 (s, 1H), 2.42 (m, 1H), 9.62 (s, 1H)

後処理

  1. customat 0° C.
  2. customThe ice bath is removed and after 15 minutes at room temperature the solution
  3. customis partitioned between ether and saturated sodium bicarbonate
  4. customThe organic phase is evaporated
  5. customto give a clear oil

出典と根拠

ORDレコード
ord-2af3065affd844bd99ccf33cda805453
出典データセット
uspto-grants-1995_05
特許番号
US05420153

関連ノート

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